


Wincest Love Week - Swesson Edition

by DeansDevilishAngel



Category: Supernatural
Genre: Angst, Boys In Love, Boys Kissing, First Kiss, First Meetings, First Time, Fluff, Humor, Implied Relationships, Implied Sexual Content, M/M, Sexual Content, Sexual Tension, Sibling Incest
Language: English
Status: Completed
Published: 2016-07-30
Updated: 2016-07-30
Packaged: 2018-07-27 14:35:58
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 10,396
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7622434
Author URL: https://archiveofourown.org/users/DeansDevilishAngel/pseuds/DeansDevilishAngel
Summary: <blockquote class="userstuff">
              <p>A collection of ficlets written for the Swesson Edition of Wincest Love Week hosted on tumblr by<br/>wincestloveweek(.)tumblr(.)com during July 2016.</p><p>For the prompt: Dean interviewing/hiring Sam.</p>
            </blockquote>





	1. The Interview

**Author's Note:**

  * For [Zetal (Rodinia)](https://archiveofourown.org/users/Rodinia/gifts).



_“Thank you for coming back for a second interview Mr… Wesson.”_ Dean Smith said as he took his eyes off the handsome young specimen seated before him and picked up the folder that held the man’s application and resume. _“May I call you Sam?”_

 _“Yes. Of course, Sir.”_ Sam Wesson shifted nervously in his chair across from his interviewer and swallowed the rest of the words trying to escape his mouth. He desperately wanted to smile and flirt with the man, see if there was any chance one of the most gorgeous men he’d ever seen was interested back but it wasn’t it just his luck? This job, if he got it -and there was a good chance since according to the receptionist he was one of only two candidates that had been granted a second interview- would allow him to finally move out on his own, away from the roommates he’d had since college. He loved them, he did, but he’d outgrown them somewhere in the last few years. The salary that came with this job would give him an independence and freedom he’d never known before. And he wasn’t going to risk that by coming on to his potential boss. He bit his lip to keep from saying anything.

Dean lifted his eyes from the papers in his hand and looked up just in time see Sam shake his head slightly and bite his lower lip. He watched the younger man for a moment noticing how he was trying to avoid looking directly at Dean and was sitting very rigidly in the chair. He smiled gently _“Sam, why are you so nervous? We like you a lot, that’s why we called you back. You can relax. We just have a few more questions about your availability is all.”_

 _“Thank you, Sir. I just, I really want this job and I don’t want to say anything that would hurt my chances at…”_ Sam looked up and lost his train of thought. Mr. Smith was smiling at him and it was breathtaking. He didn’t realize he’d stopped mid sentence until he was prompted to continue _“Hurt your chances at…?_ ” Sam found it was impossible to keep his thoughts quiet anymore _“Wow. This is so unfair. How is anyone supposed to be able to concentrate with you sitting there looking all incredible and male model-y?”_

Dean quirked an eyebrow in question but didn’t say anything in response to the man’s breathless confession.

Sam shut his eyes and whispered _“Oh my god! Please tell me I didn’t say that out loud?”_ When there was no verbal response, he opened his eyes and saw the other man give a small movement indicating that yes he had in fact said it. Sam broke into rambling at that point _“Or at least please tell me you are not offended? That I didn’t just lose this job by making a pass at the boss? Because I swear, I didn’t mean it. I mean, I did mean it. Cause you are. I mean look at you. You look like you should be on the cover of a magazine. What I didn’t mean was to come on to you. I wouldn’t… I won’t… Not ever again. I swear. Please just don’t not hire me because I said you’re gorgeous”._ Sam wasn’t aware he was pleading at that point.

Dean hid his smile. He was totally charmed by Sam but he didn’t want to give the impression that he was laughing at him. _“Sam. Breathe. It’s okay, really. It’s not the first time something like this has happened. It’s not even the worst thing that someone has said in an interview. Okay?”_ At Sam’s deep breath and nod he continued _“We’ll just forget this for now and continue on with the interview shall we? It’s really just a formality anyway. You are the most qualified candidate and we want to add you to our team. I just have another two sets of questions for you.”_

Sam relaxed and smiled back at Dean. _“Thank you. It’s really nice of you to be so understanding and willing to move past my breech of interview etiquette. I’m happy to move on with the interview. What did you need to know?”_

Dean picked up another paper which listed the job description and expectations and handed it across the desk to Sam _“As you may remember from the description, if you accept the position it will require a somewhat flexible schedule on your part that will consist of some early mornings or late evening hours and an occasional Saturday or even Sunday.”_ At Sam’s nod of acknowledgement he continues _“And that won’t pose a problem or concern for you or your family?”_

_“No Sir. It’s just me right now. I’d be free to work whatever hours or days are needed”._

Dean was pleased to hear that. He smiled and nodded to indicate he was pleased with that answer. _“I’m very happy to hear that. When would you be able to start? We’d like whomever we hire here as soon as possible.”_

 _“I’d be happy to start tomorrow but I’d also like to give my current boss some notice. She knows I’m looking so it won’t be a surprise but I’d feel bad if I didn’t give her at least a few days to find a replacement for me. So would next Monday be a good?”_ Sam’s eyes were hopeful has he talked.

 _“I think that will work out just fine.”_ Dean stood and walked around the desk, then put his hand out to shake Sam’s. When Sam stood Dean was surprised that Sam was taller than he’d first thought. _“Well, congratulations Sam Wesson. You’re hired. Sometime before Monday you’ll need to stop by HR and fill out some paperwork. Once that’s taken care of you’ll be given a key-card and shown where to set up”._

Sam dropped the man’s hand slowly, reluctant to give up the contact, and walked towards the door. _“Thank you Sir. You won’t regret giving me this opportunity. I promise.”_  As he reached for the door handle he remembered that Mr. Smith had said he had two set of questions for him so he turned back saying _“Earlier, you said you had two sets of questions. Was there something else you needed to ask me Sir?”._

Dean loosen his tie a little as he strode up close to Sam, letting his body language speak for him before given him the flirtiest most suggestive smile he could. _“Actually the second set are on more of a personal nature, nothing to do with work at all. We can talk about them over lunch if you’d like?_ ” At Sam’s huge grin and eager nod he continues _“Just to give you an idea though the first question will probably be something like ‘How do you feel about dating a ‘male model-y’ type of man?‘”_ Dean reached past Sam to put his own hand on the door handle but before turning it he looked Sam in the eye said _“At some point in the conversation I’ll probably get around to asking if you’re okay with a low-key bondage kink.”_ He was definitely close enough to feel Sam’s body tremble as he whispered _“See, I have all these spare computer cables and I’m dying to tie someone up with them”._  With that, Dean opened the door and walked out.

Sam followed without hesitation. He was definitely gonna love working here.


	2. Talk to Me

**Summary for the Chapter:**

> For the prompt: I always get your coffee order wrong because I want you to notice/talk to me.

Dean lifted the cup of coffee to his mouth, took a sip and grimaced _What the hell?_ He took the lid off and sniffed. Hazelnut? Was there hazelnut in his coffee? Again. He was starting to think that someone had it out for him. What else could explain him getting the wrong drink two to three times a week -at least. Maybe he’d just been given the wrong cup. He checked the name written on the side. A neat handwritten “Mr. Smith” was on the side. That was him so this was his!

If he ordered some complicated, frothy drink like some of the others he could almost understand. Almost. But his standard order was plain black coffee. Simple. Easy. How could it keep getting messed up? Were the interns that inattentive? Or had he offended one of the baristas? He tried to recall his last few conversations with them but nothing out of place came to mind. He probably should just let it go but damn it, the company paid handsomely for the stuff; he should at least get to enjoy his.

He really disliked abusing the interns by sending them to fetch stuff for him but the thought of facing the stack of reports on his desk without a second cup made him want to scream.

Seventeen minutes after asking his secretary to send someone for coffee he was taking a drink from a new cup. And grimacing again.

This time there was cinnamon in it. This really was too much.

Before he could consider what he was doing he was storming toward the elevator, coffee cup still in hand and into the coffee shop demanding to know from the scared young faces on the other side of counter why the hell Wesson’s Coffee Company, couldn’t hire competent help? Surely it wasn’t that hard to find someone that could pour a cup straight from the carafe? With a growled warning that if his coffee was messed up again tomorrow he’d be taking Sandover’s business across the street to Starbuck’s, he all but slammed the offensive cinnamon flavored drink on the counter and left.

He was regretting his little tirade by the time he reached the elevator.

By the time the elevator doors closed behind him, he knew he was going to have to go back and apologize. He may have had a right to be upset but that hadn’t given him the right to cause a scene the way he had.

Which is why he wasn’t completely surprised when eleven minutes after arriving back in his office his secretary rang to say Sam Wesson, of Wesson’s Coffee, was asking to see him.

Dean tells her to give him a couple of minutes then send Sam in. He spends those minutes composing a mental apology and an explanation while going over what he knows about Sam Wesson.

Tall; good looking; with dark brown hair and a body that a pro athlete would envy (if the way the polo shirts he favored was anything to go by) but also nice, quiet -to the point of being shy- if Dean’s memories of their few brief conversations at the coffee shop counter were correct.

He loses his train of thought when the door opens because while that is what greets him it’s also obvious that Sam is upset/angry. And that anger has transformed the sweet, polite guy he remembers into a whole new animal.

Sam closes the door behind him softly but in the silence of the office it sounds like it was slammed. He seems to cover the ground between the door and desk in the brief second it takes Dean to stand because before Dean can say anything Sam is standing in front of him. And even though Dean is only a couple of inches shorter all he can look at is the broad expanse of Sam’s yellow clad chest as it expands when Sam takes a deep breath before biting out the words _“Did you just. Come into my shop? Throw a bitch-fit? And upset my staff?”_

It’s a good thing that he was already planning on apologizing because he thinks if he hadn’t been he would have been in trouble -big, big trouble.

With a deep breath of his own Dean looks Sam in the eye and apologizes and tries to explain his actions. He admits he was wrong; tells him he was planning on returning to the shop shortly to apologize; he’d only come to his office to arrange for a huge edible arrangement to be delivered to the shop, for the staff, to show his regret for his verbal abuse. He promises that he won’t come back to shop, he’ll send someone else or better yet just get his coffee elsewhere.

Sam deflates before his eyes with each word he speaks. By the time Dean reaches the end of his speech Sam’s head is bent and his shoulders are shaking. Dean figures he’s about to get punched despite his sincere words. But when Sam looks up he realizes that the shaking is actually laughter not anger. He comments that he’s glad Sam can see the humor and that he hopes it means there are not going to be any lingering hard feelings between them.

That just makes Sam laugh more as he mutters under his breath _“Wow, This is so not how I hoped this conversation would go when I planned this”_ _._

 _“Did you think you’d have to drag me down there kic….“_ he cuts off abruptly as Sam’s words sink in _“Wait, did you just say you planned this? What? Why?”_

Sam blushes and seems to shrink even more into himself as he admits _“Yes, I did. I’m the one who messed up your coffee orders. But only so you’d have to come to the shop to fix it and I could see you again. Maybe talk to you.”_

Dean guesses his stunned disbelief must show on his face because Sam turns even redder and shrugs as he adds _“You used to stop by three or four times a week. We’d talk while I fixed your coffee and I really enjoyed seeing you cause you know”_ Another shrug accompanies his next words _“well, you’re gorgeous and nice. And I enjoyed your visits. Looked forward to them. But then you stopped coming in. And I really wanted to see you again. So when I realized that you were the Mr. Smith on the Sandover orders I thought, maybe, if I messed up your order you’d come down to the shop yourself to get it fixed and we could talk again. And maybe this time I could, I don’t know, maybe flirt so you’d notice me and then maybe you’d be interested enough to keep coming back and eventually one of us would ask the other out.”_

Dean’s breathless _“Oh!”_ hangs in the dead air between them for a what seems like hours but is really only a minute.

Sam must take that as his cue to leave because he makes a break for the door as he says _“Well. Um. Okay. You don’t have to come apologize… to the staff. I’ll make sure they know it wasn’t really your fault and that they shouldn’t hold it against you. And I won’t hold it against you if you do decide to switch to Starbucks. But if you do decide to give us another chance I promise your order will be correct.”_

Sam is gone and Dean is left staring at the closed door before he can gather his wits enough to form a response. He’s tempted to rush after Sam and yell that _hell yes he is interested in flirting and dating and more, so much more_. But hesitates when he remembers the last time he went to the coffee shop on impulse. He decides he should think about what he wants to say before he does anything. He doesn’t go downstairs; takes Sam at his word about the apology but he doesn’t cancel the delivery because he does regret what he did and the shop employees deserve it for how he treated them. Instead he ignores his paperwork and plans a visit to the coffee shop.

The next morning Dean paces behind his desk the whole twenty minutes it takes for the intern to return with the coffee orders. He removes the lid from his as soon as it is in his hand and sniffs but there is no strange unexpected scent drifting up from the dark liquid.  A small sip confirms it. His coffee is exactly the way he likes it. The way he ordered it.

He replaces the lid and heads for the elevator letting his secretary know that he’s leaving the office.

He waits in line for his turn at the counter silently but is not surprised to find the staff eyeing him and the cup in his hand nervously. Just as he’d hoped someone has notified Sam of his presence and it’s he who steps up to the counter when he reaches it.

Sam eyes him warily   _“Mr. Smith. Is there something I can help you with?”_

 _“Oh, I sure hope so. I was wondering if you could add some flavor?”_ Dean responds with a wink.

 _“Of course, but I thought you preferred it black?”_ Sam counters even as he reaches for Dean’s cup.

  
Dean eyes twinkle with amusement as he explains _“Not for the coffee; it’s perfect. I was hoping you’d be interested in adding a shot of tall, buff and handsome to my evening plans?”_.


	3. Creative Dating 101

**Summary for the Chapter:**

> For the prompt: I'm making you work late so let me buy you dinner.

It’s almost six o'clock and Sam is straightening up his work station getting ready to leave for the day when the call comes in.

One of the bigwigs upstairs lost an important document and needs help retrieving it A.S.A.P. The supervisor assigns it to him.

When Sam points out that his shift is about over she tells him that the suit requested him specifically if possible.

He’s about to protest again but as he takes a look around his fellow tech workers he kinda understands. At this time of day the tech support team consists of four people. An older woman, whose name he can’t recall; Paul; Ian and himself. So yeah he understands. The woman is nice enough but she’s notoriously slow and meticulous. Paul is timid and always seems overly anxious. Ian is his friend but Sam knows he’s always on the verge of being inappropriate or  offensive.

He’s in the elevator, on his way to the executive floor, before he looks at the name of the executive in need.

**DEAN SMITH _—Director, Sales & Marketing_**

An image of the man fills his mind. Early thirties, tall _(though shorter than himself)_ bright green expressive eyes, short dirty blonde hair, full lips, sharp features. In a word: _**Gorgeous**_.

They’ve never really spoken. But they’ve seen each other in the elevator. Exchanged mutual nods of acknowledgement, _‘Good Morning_ ’s and ‘ _What floor?_ ’s. And maybe some appreciative glances.

At best it’s something Sam could deem really low-key flirting.

And while Sam can’t deny that he’s interested; that he’d love the chance to see if the body under those expensive suits matches up with the football player build he’s imagined, he knows there’s not a chance. He doubts a highly educated executive would have anything in common with someone like him.

Dean Smith is out of his league.

When he arrives, he finds the secretary already gone and the door to Mr. Smith’s office open. His knock is greeted by the sight of the man waving him in while he finishes his telephone conversation before he addresses Sam. _“I’m glad you were still here. Thank you for coming promptly. I know it’s late and I hate to  disrupt your plans for the evening but I didn’t want to put this off another day.”_

Sam nods in understanding _“It’s not a big deal. The microwave pizza and beer will still be waiting when I get home. Now, what are you having a problem with Sir?”_

Mr. Smith grimaces _“Well for starters you calling me ‘Sir’. It makes me feel like you’re talking to your father. I’m not that old. My name is Dean”_.

Sam laughs; The man is right, there is probably only four or fives years difference in their ages _“Okay **Dean**. What seems to be the technical issue you are experiencing?” _

Dean’s voice sounds like it’s mocking him _(but in friendly joking way)_ as he repeats back _“_ _Well **Sam** , the **issue** is that earlier today I sent a very important quarterly marketing report to the printer. Or at least I thought I did. But when I went to pick it up; it wasn’t there. Now I can’t find the report anywhere on my computer.”_

Sam opens his mouth to ask if he’s checked in the deleted files when Dean cuts him off _“Before you ask- yes I checked the deleted files before I called Tech Support. I didn’t see it there either. That’s why I called”_.

Sam sets down the small case containing his computer tools before asking _“Mind if I come around and have a look for myself? Or do you want me to try and talk you through finding it?”_

Dean nods and rolls his chair back, away from the desk, but remains seated as he gestures for Sam to help himself.

Once he’s in front of the screen Sam leans down and with a few clicks has pulled up the deleted file folder;expanded the info section to show the last date each file was accessed. The file he is looking for is not there. A couple more clicks indicates that the report is not backed up in the printer’s queue (which wouldn’t solve the problem of the missing report but maybe it would eliminate the urgency).   _“Mr. Sm..Dean, this is going to take a bit. I’m going to have to run a search of the hard drive for your document but I’m going to need some information for the search parameters from you”_.

Dean rises from his seat even as he’s saying _“Let me get out of your way so you can get to work.”_ As he slides behind a still leaned over Sam, his hips press firmly but briefly against Sam’s ass. And either Dean is turned on or he’s huge because Sam can feel the outline of his dick and barely keeps himself from pressing back against it. If he didn’t know any better he’d swear it was deliberate.

If Dean apologizes Sam doesn’t hear it through the roar of desire that courses through him. 

But when Dean reaches the other side of the desk and is facing him again there is nothing but polite friendliness in his smile. Sam pulls up the chair that Dean had just vacated and sits to begin the search.

Just as Sam is finished typing in the report name that Dean has given him to search for there’s a knock at the office door. Sam looks up from the screen to see a young man with a couple of white paper bags standing in the doorway and Dean reaching into his pocket for his wallet.

Once the delivery guy has left Dean sets about clearing a space on the desk and setting an  enormous amount of food containers and a six pack of beer between them. Sam watches until Dean picks up a set chopsticks and holds them out to him as he asks _“I hope you like Chinese?”_

Sam can feel his head nodding to indicate that he does but when he makes no move to take the chopsticks Dean pulls his hand back and says _“Would you prefer a fork?”_.

Sam takes the fork and the container of chow mein automatically but waits for Dean to pop open two bottles of beer and take a seat himself before taking his first bite. There’s something off  about the whole thing but he can’t quite put his finger on what it is.

They eat while the search runs and they talk about growing up, school, sports, movies, books -everything. And find that they have quite a bit in common. By the time computer dings to signify the end of the search Sam still hasn’t figured out what feels wrong; he’s too busy enjoying it.

Dean starts cleaning up their meal as Sam turns his attention to the screen. But what he sees doesn’t make sense.

_**No Items Match Your Search** _

He lets out a loud huff of air. He’s probably going to have to search through each file manually to see where the report ended up.

When he says as much Dean just walks around the desk and perches on the corner as he points out that it’s after seven-thirty and they should probably just call it a day.

 _“But what about the report? I thought you needed it for the meeting in the morning?”_ he inquires confused as to why Dean doesn’t seem upset.

Dean leans toward Sam as he reaches around him to the credenza behind the desk as he whispers _“Well, I’ll just come in a little early tomorrow and print it from the flash drive I saved it to.”_  When he pulls back there’s a key ring, complete with flash drive, in his large hand.

Sam actually sputters _“What? You’ve had it all this time? So why?”_ As he looks around again it all falls into place.

The last minute call for support. The request for him specifically. The large amounts of [pre-ordered] food. The lack of report to be found.

It looks like Dean went through all this trouble just so they could have dinner together. It’s set up to feel almost like date. But he needs to make sure before he says or does something that will get him fired or accused of harassment.  

 _“You know you could have just asked me out instead of going through all this”_ he waves his hand around.

Dean gives a slight shrug of his broad shoulders as he explains _“I know. But as I’m sure you’re aware, Sandover’s has a non-fraternization policy regarding its employees. So I had to do a little creative recognizance to make sure you were interested before I went risking my future with this company by asking you out.”_

Sam lets out a full body laugh as he grabs Dean by the loosened tie and hauls him closer _“I’d say your covert mission is a booming success”_ he manages to say before pressing their lips together.

Many minutes later a breathless Sam pulls away enough to whisper _“Thank goodness for creativity”_ against Dean’s lips _._

Dean whispers back just as breathlessly __“You ain’t seen nothing yet Sammy. Just wait until my computer breaks down again next week and I show you what I can do with a couple of computer cables and a can of whipped cream.”__


	4. Dean Needs a Wedding Date

**Summary for the Chapter:**

> For the prompt: My parents are coming to town and I told them I have a boyfriend (aka Fake Boyfriends).

**Notes for the Chapter:**

> Just want to point out (in case it's not clear) that the conversation at the very beginning is Dean on the phone with his sister and we are only hearing his side of it.

Dean hisses _“Hold on a second”_ then presses his cell phone to his chest as he ducks into the men’s room. After glancing around to make sure he’s alone -all the stall doors are slightly ajar- he puts the phone back to his ear. _“I told Mom I was seeing someone last month Jo. We were all together for your engagement announcement and I figured that would keep her off my back for a while.”_

_ “I understand she and Dad worry about me -that’s why I lied!” _

_ “Well I didn’t know then that you and Ash were going to set a date so quickly. I figured you’d have a nice normal long engagement like everybody does. Then in a few months, right before the wedding, I could tell her we broke up. And then she’d stop pestering me to find someone while I got over it”. _

_ “Come on Jo. Not you too. I get enough from Mom. I’m not lonely or heartbroken or anything like that. Relationships take time and commitment. I’m just too busy right now to be able to give one either of those.” _

_ “I guess I could say he’s out of town this weekend but then what excuse would I give when he doesn’t show up at the wedding? There’s no way they’ll believe it both times.” _

_ “I love you little sister but this wedding is turning into a big pain in my as… Okay, okay. Thanks for the heads up about mom and dad’s visit this weekend. I owe you.” _

If there had been a way to aggressively hang up a smart phone Dean’s sure he would have ended the call that way. Instead he settles for shoving the phone angrily into the breast pocket of his suit jacket. He sets his hand on the counter in front of him and bends his head, lets himself think. There’s got to be some way he can get out of this mess without admitting he lied. That will just convince his mother that she is right to worry about him and lead her into thinking she need to be more involved in his life than she already is. 

The quiet _“Excuse me”_ from behind him has him spinning around so fast he knows that if it hadn’t been for the counter supporting him he would have fallen on his ass.

He eyes the very tall man (who appears to be trying to shrink in on himself) in disbelief, then the door to the restroom that’s on the wrong side of the room from where the man should have just entered _“Where did you come from?”_ but in his gut he knows the answer -the man has been there along.

Tall guy tilts his head to indicate he came from one of the stalls, just as Dean had feared. He motions with his hand to indice that he wants to approach the sink and use it. 

Dean steps aside to give him access. Every cell in his body is telling him to just cut and run but he resists the impulse. He knows what large companies like this are like. There’s always talk about/among the employees. Who is dating whom or sleeping around or getting married/promoted/dumped/fired. There’s always someone or something to talk about. And Dean just gave out some choice gossip fodder. To a tall man -who’s employee badge identifies him as Sam Wesson in what’s, if he remembers correctly, the standard yellow polo for Sandover’s technical department. 

He needs to know how bad it’s going to be _“Just how much of that did you overhear?”_

_ “Your little sister, Jo, who is getting married next month, called to tell you that your parents are arriving for a surprise visit this weekend during which they’ll expect to meet your new boyfriend, who doesn’t actually exist -because you don’t have time for a relationship- and now you have to come up with believable reasons why he won’t be in town this weekend or available for the wedding next month.” _

_“So every word then?”_

When tall, yellow-shirted Sam meets his eye in the mirror and indicates yes, Dean closes his eyes briefly and lets out a _“Well that’s just perfect”_ under his breath. There’s not much he can do to stop it at this point. His best hope, since he’s fairly new to the company, is that this guy doesn’t know who he is and that when the story gets relayed to others he’ll just be “some exec” instead of the sales and marketing director. 

Dean take a breath, collects himself, straightens his tie, nods at the Sam and turns toward the exit.

He has one hand on the door knob when Sam speaks again. _“Mr. Smith?”_ Dean stiffens his spine not quite sure what to expect because obviously the guy knows who he is. He’s totally shocked by Sam’s next words _“You don’t have to worry. I’m not going to say anything about this to anyone.”_

Dean whips his head around, distrust in his eyes. He knows he should just say Thank you and hope Sam is being sincere. Instead he finds himself asking why Sam would do that for him.

Sam says that it’s none of his business what Dean does outside of work and he doesn’t think that it’s anyone else’s either. He goes on to explain that he’s new to Sandover's (three weeks) and gossiping about one of the V.P.s doesn’t seem like a good way to start a new job. 

Dean thanks Sam, offering to pay for a pizza or at least a round of beers, to show his gratitude. Sam declines both saying as he walks past Dean and out of the restroom that he wishes he could do more to help.

As the afternoon passes Dean finds himself thinking of Sam quite a bit. Now that he’s not reeling from the embarrassment of being caught lying to his Mother like a pre-teen he can appreciate how attractive Sam Wesson is. He also can’t stop himself from recalling Sam’s parting words. Dean hasn’t dedicated much time if any to coming up with a solution for his situation. He needs to throw out some theories and ideas to see what sounds believable but he can’t do it alone; he’s the worst at seeing the plot holes and downfalls of his own plans. He’ll need some help. 

Since is Sam the only one besides his sister who knows of his dilemma, and he’s on hand Dean’s on the phone dialing Sam’s extension before he can double think it. _“I need to see you in my office as soon as possible.”_

When Sam arrives he’s led into the inner office immediately per Dean’ instructions.  As soon as the door closes they both speak at once

_ “I was wondering if you could help me come up with a believable excuse” _

_ “I’ve been thinking and I have a suggestion on what you could do” _

~*~*~*~*~*~*~*~*~

Dean’s sitting in the restaurant with his parents wondering how much longer it’ll be before they question if his boyfriend is real or not and questioning why he let himself get talked into this.

If he’s honest he hadn’t put up much of a fight the day before when Sam’s helpful suggestion had turned out to be for Dean to bring someone to meet his parents that weekend then use the out of town excuse for the wedding, then stage a breakup soon after. He’d put up even less of one when Sam had suggested that he himself could be said date/boyfriend. It’d made sense when Sam had explained it. And they’d spent some time yesterday and earlier this morning exchanging information about themselves and fleshing out their “how we met” story (Dean shot down the “Met at the health club” one and Sam almost walked out when Dean suggested the “I heard him scream and rescued him from what he thought was a ghost” approach).

Dean had been feeling pretty good about their chances of fooling his parents for the weekend when he’d left to meet his parents at his house. But now Sam is forty minutes late for their reservation and Dean is beginning to think he’s been set up.

Sam proves him wrong by appearing exactly two minutes after Dean thought it. He’s breathing a little heavily and looking a bit flushed as he explains the series of things that delayed him. A tech problem that kept him later than expected at the office; traffic on his way home to change [into collared shirt and jacket]; having to park a block and half away from the restaurant [Dean used the valet].

After they’ve ordered things settle into that awkward silence that is common among strangers at first meetings and Dean thinks their endeavor is going to fail anyway. But Sam surprises him by breaking the ice with his mother. _“Mrs. Smith? Can I be forward and ask you something personal?”_

Dean chokes on his drink of water and his parent turn round, inquiring eyes to their son’s ‘friend’.

_“Was Dean this pretty as a child or has he had plastic surgery?”_

Dean glares at Sam while his father tries to rein in his laughter and his mother’s smile widens. Sam’s reaction to Dean’s glare is to reach out and pat Dean’s leg and softly say _“I’m sorry Babe. I couldn’t resist.”_ Dean has no choice but to smile back as sweetly as he can manage and resist the urge to tell Sam he’s 'this close' to being fired. Meanwhile, Sam has continued as if it’s a normal occurrence _“He just gets so offended at being called ‘pretty’ you know? So let’s pretend for his sake that I said handsome.”_

Dean’s mom beams at Sam and breaks into stories about how blonde Dean was as child, his cheer-leading days and other embarrassing things.

Dean can’t complain because Sam is charming his parents right before his eyes. So much so that they are on first name basis by the end of the meal and Ellen is insisting that Sam join them the next day for a nice home-cooked meal.

~*~

The next afternoon Dean watches as Sam continues to win his parents over with witty and clever anecdotes about his life and his travels across the U.S. with his father and thus keeping the conversation from straying into questions about ‘their relationship’ too often.

His parents do manage to get in a few however. They answer the “how did you meet?” one with their prearranged answer about meeting in the elevator. Sam even goes the extra mile adding the detail of how nervous he’d been since it was his first day at Sandover’s and how happy he’d been to get such a warm welcome.

Dean even manages to contribute with a saccharin laced _“Well look at him. Can you blame me for scooping him up before anyone else saw him?”_

The only real trip-up comes when it slips out that it’s Sam first visit to Dean’s house (which would include his bedroom). His parents eye them suspiciously for a moment because they know that is atypical of Dean (three weeks of dating and no sex? Not his usual M.O.) Sam saves them by putting on a blushing, stuttering, shy performance about how since they work together they wanted to take things slow; get to know each other well before taking the next step, blah blah blah.

Dean’s pretty sure that’s what convinces his mom that Dean is finally, really, truly, serious about someone.

And it’s so obvious that she couldn’t approve more of his choice that he’s not the least bit surprised when she personally extends an invitation to Sam regarding the wedding. What does surprise him is that Sam doesn’t even try to decline; he in fact promises to do his best to be there.

When he finally gets Sam alone -on the walk out to his car so they can ‘say good night in private’- Dean losses no time demanding to know what the hell Sam thinks he’s doing. He’s supposed to be helping Dean, not digging him in deeper.

Sam explains that he’s giving Dean options. Dean can make an excuse for Sam’s absence later or run with the plan and bring Sam along to Hawaii for the wedding (Ellen had talked about the ‘Destination Wedding’ several times during the afternoon).

Dean can’t help but question Sam’s motive’s _“Why are you being so nice? What’s in this for you?”_

Sam looks at him like he’s stupid _“Let me list the reasons for you. I’d get to spend more time with your parents; they’re great by the way. I’d get a free trip to Hawaii; who could down that down? I’d get to spend time with a handsome, educated, well-to-do man and get to call him my boyfriend to boot. I’m not really seeing a downside here.”_

With a nod of understanding Dean goes on _“Well that’s great for you. But I’m not really seeing what’s in it for me.”_

Sam leers at Dean as he explains _“For starters you wouldn’t have to worry about what to tell your parents. You wouldn’t have to deal with questions all week-end about why your boyfriend isn’t there. And with us having supposedly been ‘dating’ for two months by then no one will be surprised by us sharing a room. But if you need more consider this; I’ve always wanted to have sex on a beach. Can you think of a better place to try it than Hawaii?”_


	5. The Post-It Note Bandit

**Summary for the Chapter:**

> For the prompt: Someone's leaving post-it notes with cheesy pick up lines for me everyday.

The first note falls out of the workroom refrigerator with his lunch on Monday. He thinks it’s meant for someone else. But with no way to tell who exactly he can’t in good conscience put it back. He decides to throw it away and save both sender and intended recipient from the embarrassment of the cheesy pickup line.

Sticking the note in his pocket to dispose of later he goes to join his co workers for lunch.

When he finds the second one on his desk and everyone in the tech department claims not to have seen who put it there he becomes convinced it’s Ian playing a joke on him (with pilfered office supplies).

The third one is in his work mailbox and he wonders how many more he’ll find before the joke gets tired and played out.

He finds a fourth one on his car window.

 

 

 

 

 

 

 

When he finds another one on his desk upon arrival Tuesday morning, but Ian isn’t scheduled for another hour, he realizes he has an admirer among his co-workers.

The notes keep showing up. Three a day. Everyday. Like clockwork. On his lunch. On his desk. In his mailbox.

 

And no one ever sees who left them.

 

 

 

 

Despite the cheesy nature of the notes Sam can’t deny that by Thursday he’s very flattered and totally & completely intrigued. Someone (who appears to be part ninja) has gone through great effort to get his attention and he really hopes he’s not disappointed when (or if) he finally finds out who it is.

 

 

 

Which is why he’s crushed to not find any notes on Friday.

There isn’t one on his lunch. Nor in his mailbox (regardless of how many times he checks it). There has not been one on his car since the first day. His desk remains conspicuously empty of colorful post-its too.

Until he returns from dealing with his last ticket of the day. And sees the bright green note waiting for him. Suddenly, the end of the day can’t get there fast enough.

 

 

 

At first he can’t believe what he sees at the bar. He actually thinks seeing Dean Smith the incredibly gorgeous sales and marketing director there is just a huge coincidence. (The bar is not that far from the office and he knows it’s a popular hangout for the after work crowds.) Until Dean walks right up to him and with a shy, embarrassed smile hands him the last note.

 

 


	6. Drunk Love

**Summary for the Chapter:**

> For the prompt: Drunk at the company dinner party.

Sam Wesson is at his first Sandover company party. It’s probably going to be his last too.

Attendance hadn’t been required even if it was highly encouraged. But with it being the first one since he’d been hired he’d decided to attend. And honestly everything had been fine, if somewhat dull, until he’d started drinking.

The food itself had been delicious and plentiful. In his opinion buffet style was always a good choice. The company at his table _(his fellow tech workers)_ had been entertaining and enjoyable.

But then the alcohol had started flowing pretty freely.  He’d always been a bit of a light weight, especially considering his size. He should have known well enough to stick to beer instead of indulging in stronger stuff. But as his co-workers pointed out how often did they get to drink on the company’s dollar?

Even so, he should have followed his instincts and left when Ian suggested they play a game of truth-or-dare to _‘help liven things up a bit’_. The fact that he hadn’t should have been his first clue that he’d already had too much.

But it had started off harmlessly enough. Lily had chosen truth and confessed to having a crush on one of the executives. Ian, who had chosen truth also, had confessed to not having lost his virginity until he was twenty one. Jake had chosen dare and been challenged to kiss the next person who walked by. Luckily for him it had turned out to be one of the older secretaries and she’d taken the kiss on the check and the explanation of ‘tag you’re it’ in stride. Each person going in turn around the table until finally it had been Sam’s turn.

He’d chosen dare. He should have chosen truth.

Because now he’s weaving his way to one of the bars in corner, a list of dirty sounding drinks running through his mind _(courtesy of Ian)_.

He knows he really should just go home _[fuck what everyone else says or thinks]_ because ever since he stood up things started to look blurry and sound faraway. But then he bumps into someone and he realizes he’s reached the bar and the white shirted person in front of him _**[why’d the bartender take off the red vest?]**_ turns to face him _ **[why is the bartender on the same side as him?]**_ and asks if he can help with something so Sam blurts out the first drink he remembers from the list Ian gave him _“Iwantablowjob”_.

The floating emeralds in front of him _**[where’d those come from?]**_ seem to get larger and there’s a male voice saying _“Excuse me?!”_ So he repeats his order _“I’d like a blow job… please.”_ And then the voice is asking him _“Are you drunk?”_ Sam can feel his head shaking in the ‘no’ motion but he’s giggling and a voice that sounds very much like his own is saying _“wouldn’t be ordering a jow blob if I wasn’t”_.

He feels a large, strong hand close around his bicep, pulling away from the bar and that voice is saying _“I think you’ve had enough to drink tonight. Let’s get you back to your friends”_.

On the walk back to his table things get even hazier but the voice is asking where his things are and his friends are suspiciously quiet outside of a few ‘ _Yes, Sir_ and _No, Sir_ ’s and his own voice whining fairly loudly _“wouldn’t give me a blow job thingie even though I said please”_.

Then there’s the feel of fresh air and what he thinks is the movement of riding in a car.

And then softness. And darkness, blessed, blessed darkness.

He wakes up with a pounding headache. In a room he doesn’t recognize. And even though the sheets on the king-sized bed he is in feel like the best thing ever, he knows he can’t stay.

After reluctantly and slowly swinging his legs over the side and managing to sit mostly upright he sees a bottle a water, a bottle of aspirin and a note indicating that he’s welcome to take a shower and change into the clean clothes left for him in the bathroom and that there will be coffee and bagels waiting.

That’s when it hits him that he’s in a stranger’s bed wearing only a t-shirt and boxer briefs.

A quick mental cataloging of his body indicates that he didn’t have sex _**[thank god for small favors]**_ because outside of the headache and severe cotton-mouth he feels fine.

Knowing he can’t put off facing whoever is waiting for him to emerge he downs the pills and water and heads to the restroom.

The hot shower and mouthwash do a tremendous job in helping him feel like he can face what he’s now sure is the man he came with last night _(going by the products in found in the bathroom)_.

Dressed in the clean t-shirt _(it’s maybe half a size too small for him)_ , brand new boxer briefs and clean socks that were left out for him and his pants from last night he opens the bedroom door and follows the scent of coffee to the kitchen but stops cold in the entry way.

There’s man standing at the counter, facing away from him, pouring a cup of coffee from the half-full carafe. But Sam doesn’t need to see his face to know who it is. The the height, broad shoulders _(even clad in a black t-shirt and lounge pants instead the usual suit)_ and close cropped _(un-styled for once)_ dirty blonde hair give it away.

Sam has to swallow twice before he feels like he can speak _“Umm, Mr. Smith? I’m just going to go ahead and leave if that’s okay?”_

Dean Smith, Director of Sales and Marketing for Sandover’s turns bright green eyes on him _**[that explains the image of emeralds he recalled while showering]**_ and gestures toward the table   _“Nonsense Sam. You need to have some coffee and a bite to eat before you go. And I think, considering what happened last night, that you can call me Dean now”._

Sam’s jaw drops because it sounds like Mr. Smith is implying that they did ‘something’ last night _**[not actual sex -Sam’s pretty sure of that]**_ but something _“Oh, umm… Wow! Did we …? I mean did you …? Because I don’t really remember much of what happened last night after I got up to order the drin… Oh fuck! How much trouble am I in?”_

Dean laughs _“Probably not much if any. Mr. Adler was pretty tipsy himself and I got you outta there before anyone else noticed. By the way, you really should tell your friends where you live. Not a single one of them could tell me your address. That’s why I brought you home with me, well mostly why.”_

He holds out the cup in his hand to Sam before turning to pour another one. _“And about last night; Nothing happened. But IF it had -trust me **you’d** remember. Now sit down and eat and I’ll answer all your questions. And Sam? When you’re sober … we **are** going to talk about the blow job you asked me for.”_


	7. You Can Be My SugarDaddy

**Summary for the Chapter:**

> For the prompt: Sugar Daddy

**Notes for the Chapter:**

> This ended up being a continuation of the "Fake Boyfriends" ficlet posted in Chapter 4.

The four weeks between meeting Ellen & Bobby Smith and flying to Hawaii with Dean for his little sister’s wedding were some of the best Sam Wesson could remember having.

They’d spent time together fairly regularly what with going to lunch two or three times a week and dinner at least once a weekend (not that what Dean did really counted as eating in Sam’s opinion) all in the guise of getting to know each other well enough and being comfortable enough with each other to be able pass as an established couple for an extended weekend with Dean’s relatives. They’d decided that since Dean was not a big believer in PDAs (Sam wasn’t either really) that lots of hand holding and small, brief pecks on the cheek or lips would suffice for their charade. And maybe nicknames. So they focused on those things and Sam quickly realized that he enjoyed the feel of Dean large strong hand in his and loved the feel of his plush lips against Sam’s cheek or own lips. It didn’t really take long for the weight and warmth of Dean’s hand on his lower back as they left or entered a room to feel completely natural.

As if by mutual agreement, neither mention the intention of sharing a room or the proposed sex on the beach. But Sam was pretty sure that neither one of them had forgotten.

There’d also been a trip to a local theater for a production of ‘Our Town’ (Sandover’s had a small section of seats each season for all for its executives to use and Dean hadn’t been able to refuse the invitation from a higher up) and a retirement party for a man in Dean’s department that he’d been required to attend (and brought Sam along as his date).

But surprisingly the times Sam had enjoyed most had been the weekend afternoons spent at Dean’s house eating pizza (or some other form of take out), drinking [lite] beer (no more than two for Dean), just talking while some sporting event played out on the large screen television Dean owned but never really watched.

They’d discovered more things in common than Sam had ever imagined they could have.

The weekend before the wedding had been especially fun. Sam had asked during their Friday night dinner (at some expensive French restaurant that Dean had insisted on) what he should pack for their trip. They’d conclusion that Sam’s usual jeans and flannel shirts were not climate appropriate. Finding out Sam didn’t own any shorts or polo shirts that weren’t embossed with Sandover logo had led them to a Saturday morning shopping spree that Dean had insisted on paying for claiming that Sam wouldn’t be spending the money if it wasn’t for the wedding. They’d had fun and at one point Sam had quipped that all they’d needed was a Roy Orbison soundtrack to make him feel like Julia Roberts in Pretty Woman which had sent them both into fits of laughter.

~*~

The long flight to Hawaii and subsequent dinner with Dean’s family had left them exhausted and they had excused themselves shortly after the meal was over to retire to their shared room.

Sam had taken the offered first shower and unknowing what expect from their first night of sharing a bed had tried to mentally prepare himself. He needn’t have worried because Dean had emerged from his turn in the restroom clad in a pair of sleep pants and t-shirt, walked past Sam with a softly murmured ‘Good Night’, gotten in the bed, turned off the lamp on his side and laid down. It wasn’t until Sam had done the same that Dean had whispered into the dark _“I’m glad you’re here with me Sam.”_

The next day had consisted of a late breakfast with the all the arrived guests at that point. Afterward they had given into the bride-to-be’s pleas to join in the swim-with-dolphins adventure she had planned.  

The afternoon had been fun and Sam had really enjoyed getting to know Jo and Ash better. The day flowed smoothly and before Sam knew it the rehearsal dinner dinner was over and he and Dean had been coaxed into hanging out at the poolside bar with several other couples. That’s  where things started to change between them. Sam’s not sure if it was being in the company of friendly happy people or the drinks they indulged in as the evening progressed but by the end of it the the causal touches and kisses they had practiced for their charade had progressed into spine melting kisses and just-shy-of-groping touches.  

The elevator ride back to their room had seemed to kill the desire, at least in Dean, because he’d put on a repeat performance of the previous night. Only this time Sam had already been in the bed. Once Dean had joined him and turned out the lights he had once again turned to Sam and spoken _“How much did you have to drink?”_

Surprised by the question, Sam had stuttered a _“What? Why? I’m not drunk. I wouldn’t embarrass you like th…”_

Sam felt Dean sit up and lean over him _“Sam I don’t care what most of those people think. I just want to be sure you’re okay with this”_. And with that he had leaned down and taken Sam’s lips in a heated kiss waiting until Sam had moaned in approval before moving to lay on top of Sam,  pressing him into the mattress. But they were both too keyed up from the weeks they’d spent ignoring the tension between them for it to last long. Sam came almost as soon as Dean touched his bare cock and had given into his own orgasm a minute later. Though neither one of them had spoken much as they’d cleaned up, they had fallen asleep pressed together in the middle of the king size bed.

The wedding day had started off with a frantic call from Ellen and hadn’t given them much opportunity for private conversations as the flurry of last minute preparations had kept Dean busy. Sam had spent most of the day, until the ceremony actually, chatting with different family members who wanted to know all about him and how he met Dean. With the exception of one cousin, (who hinted that she thought he was using Dean for his money) Sam had enjoyed visiting with Dean’s family even though he’d probably never see any of them again.

It wasn’t until after the simple but beautiful ceremony was over and the reception was winding down that they found the time to do more than smile and ask each other if they were doing okay or needed anything.

They’d excused themselves from the remaining guests and Sam thought they were heading for the hotel lobby when Dean had suddenly griped his hand tighter and pulled him along a sidewalk that lead to the hotel’s private beach area.

They been walking leisurely along the sand just enjoying the sound of the surf when Dean had again tightened his grip on Sam’s hand and tugged him along, this time towards one of the tented cabanas that were provided for guests use. He’d pushed Sam up against the canvas and drawn him into a kiss that left Sam breathless, then pulled back slightly to give his hands access to Sam’s belt and zipper. Then he’d murmured against Sam’s lips “I know this isn’t exactly what you described but I hope it’s a close enough second that it will fulfill your sex-on-the-beach requirements.” Before dropping to his knees on the sand and running his tongue over Sam’s half-hard dick. Sam is not too embarrassed to confess that he came pretty quickly for the second night in a row. And it wasn’t all because he’d been dreaming about Dean’s lush lips sucking him off (among other things) for a month but more about the fact that Dean was willing to set aside his _‘no PDAs’_ rule in order to give Sam something special.

Their return to the room had probably been quite entertaining to anyone watching. Dean had been (understandably) interested in returning to their room as quickly as possible to resume their private activities (in private) while Sam had just been trying to gather his wits and stabilize his wobbly knees so he could walk properly.

In the pattern established on the two previous nights Sam had been given the right to first shower but had coaxed Dean into sharing instead.

What followed was a lot less of an exercise in washing than it was an excuse to run their hands over the others naked body. Until finally Sam couldn’t wait any longer and dragged Dean out, pausing only long enough to dry them both off sparingly, before finally pushing Dean on to the bed and climbing into his lap. As much as Sam was enjoying Dean’s prep and wanted to drag out the journey to his second orgasm of the night he was quickly reminded that Dean had yet to have his first _“I’m really close. I don’t know how much longer I can last Sammy”_.

And he hadn’t been exaggerating either -he’d white knuckled through Sam sinking down on his cock before he’d bucked up a half dozen times and come. And disappointed as Sam could have been he hadn’t actually been able to complain when after disposing of the condom Dean had crawled back in bed, rolled Sam on his back, pinned him there with an arm across Sam’s hips while he’d taken is time getting Sam off again with his mouth and hands.

They’d fallen asleep wrapped around each other again until Sam had woken Dean up in the early hours with his hand wrapped around Dean’s already hard dick, whispering that Dean was one orgasm behind and needed to be caught up.

As a result of their dawn activity they’d overslept and had to rush to the airport in order to make their flight. Their late check-in had resulted in an aisle between them on the return flight which had made discussion of their ‘vacation’ difficult even if they’d wanted to address it.

Most of the trip from the airport to Dean’s house, where Sam had left his car, had been spent with Dean on his phone catching up on his missed emails and work messages.

When Sam had made to leave (hoping Dean would ask him to stay) Dean hadn’t tried to stop him instead he’d asked if they could meet for lunch the next day to discuss what reason he’d give his family for their break-up.

Hurt beyond his ability to stay quiet Sam had snapped out _“Just tell them I left you because you’re an insensitive asshole”_ and left before Dean could wipe the hurt look off his face and form a response.

He regretted letting his anger get the best of him before he was back to his apartment.

~*~

The next morning he’d been surprised when his first call of the day was from Dean _“Can I see in my office right away? I need to talk to you”._

Sam had barely opened the door when his words came tumbling out, apologizing for his words from the night before.

When Dean had asked why Sam had gotten so upset by his question Sam had done his best to explain _“I know it was supposed to all be pretend, just for the weekend. But I’ve really enjoyed the time we’ve spent together getting to know each other. And I guess I thought that night on the beach was more than just sex; that there was something between us.”_

He’d been happily surprised to hear Dean admit to feeling the same _“I know what you mean; I’ve felt it too._ “ Then crushed when he’d continued _“But Sam, nothing has changed for me. What I told Jo on the phone still stands. I don’t have time for the kind of commitment that those type of relationships seem to require. I’ve tried before. They just never seem to work out for me.”_

With hope blooming in his heart Sam had assured Dean that he could deal with it _“I’m not saying it would be easy but I wouldn’t be expecting for your life to suddenly revolve around me. We could just keep doing what we’ve doing for the past few weeks. Having lunch together, going out to dinner, hanging out at your house on weekends when you don’t have to work. See where it leads us.”_

 _“And you’d be okay with that?”_ Dean asked.

  
Sam couldn't stop the happy smile from crossing his face “Of _course. What’s the down side for me? Expensive dinners. Shopping sprees. Long weekends away now and then. -I’ll just tell everyone you’re my sugar daddy”._


End file.
